Skirgaila, also known as Ivan/Iwan ( or 1354 – 11 January 1397; baptized 1383/1384 as ''Casimir''), was a regent of the Grand Duchy of Lithuania for his brother Jogaila from 1386 to 1392. He was the son of

Algirdas Algirdas (; , ; – May 1377) was List of Lithuanian monarchs, Grand Duke of Lithuania from 1345 to 1377. With the help of his brother Kęstutis (who defended the western border of the Duchy) he created an empire stretching from the pre ...

, Grand Duke of Lithuania, and his second wife

Uliana of Tver Uliana Aleksandrovna ( – 17 March 1391) was a grand duchess of Lithuania as the second wife of Algirdas. She was the daughter of Alexander of Tver and Anastasia of Galicia, daughter of Yuri I of Galicia. Life After her father and eldes ...

Biography

After Algirdas' death in 1377, Jogaila became the Grand Duke. It is believed that the dynastic disputes that soon erupted between him and his uncle

Kęstutis Kęstutis ( – 3 or 15 August 1382) was sole Duke of Trakai from 1342 to 1382 and List of Lithuanian monarchs, Grand Duke of Lithuania from 1342 to 1382, together with his brother Algirdas (until 1377), and with his nephew Jogaila (from 1377 to ...

and his cousin Vytautas the Great were largely inspired by Skirgaila. It is known about his travels to the

Teutonic Knights The Teutonic Order is a Catholic religious institution founded as a military society in Acre, Kingdom of Jerusalem. The Order of Brothers of the German House of Saint Mary in Jerusalem was formed to aid Christians on their pilgrimages to t ...

in 1379 just a year prior to the controversial Treaty of Dovydiškės. Skirgaila was the chief supporter of his brother Jogaila and helped him to imprison both Kęstutis and Vytautas in Kreva castle during the

Lithuanian Civil War (1381–1384) The Lithuanian Civil War of 1381–1384 was the first struggle for power between the cousins Jogaila, Grand Duke of Lithuania and later King of Poland, and Vytautas the Great. It began after Jogaila signed the Treaty of Dovydiškės with the Teut ...

. Some historians speculate that Kęstutis' death after a week in prison was in fact assassination carried out by Skirgaila. As a reward for a job well done, Skirgaila received the

Duchy of Trakai Duchy of Trakai () was a subdivision of the Grand Duchy of Lithuania during the 14th and early 15th centuries. The Duke of Trakai was an important position held either by the Grand Duke of Lithuania himself or his second-in-command. History After ...

. When Jogaila was preparing for the Union of Kreva, Skirgaila was actively involved in the negotiations and even headed a diplomatic mission to Poland. The negotiations succeeded and Jogaila married

Jadwiga of Poland Jadwiga (; 1373 or 137417 July 1399), also known as Hedwig (from German) and in , was the first woman to be crowned as monarch of the Kingdom of Poland. She reigned from 16 October 1384 until her death. Born in Buda, she was the youngest daught ...

and was crowned as

King of Poland Poland was ruled at various times either by dukes and princes (10th to 14th centuries) or by kings (11th to 18th centuries). During the latter period, a tradition of Royal elections in Poland, free election of monarchs made it a uniquely electab ...

in 1386. He appointed Skirgaila on 13 March 1386 as governor in Lithuania, not only on his behalf but also on behalf of queen Jadwiga and Polish Crown.Frost 2015, p. 77. As ruler of Lithuania, Skirgaila had to deal with his oldest brother Andrei, who still was refusing to accept Jogaila as a Grand Duke. First he defeated Andrei's ally Sviatoslav II of Smolensk in a battle of the Vikhra River near Mstislavl on 29 April 1386, during which Sviatoslav lost his life. Sviatoslav son Yury of Smolensk was forced to accept Lithuanian suzerainty in exchange of princely throne. Later Skirgaila attacked Polatsk; his first expedition in October was unsuccessful, but the next on March 1387 resulted in Andrei's capture and death of his son Simeon, who was killed in a battle.Frost 2015, p. 78. Next month Skirgaila was invested in Polatsk and once again pledged his loyalty to Jogaila, Jadwiga and Polish Crown, promising return of his land in case of his heirless death. Skirgaila was now directly ruling over large portion of Lithuania, including the duchy of Vilnius, ruled on behalf of Jogaila. On February 20, 1387, Jogaila elevated his brother above other Lithuanian princes and extended his authority over Ruthenian lands. In 1389, he started a new civil war, but after an unsuccessful attack on

Vilnius Vilnius ( , ) is the capital of and List of cities in Lithuania#Cities, largest city in Lithuania and the List of cities in the Baltic states by population, most-populous city in the Baltic states. The city's estimated January 2025 population w ...

he had to seek help from the

. In 1392 Jogaila and Vytautas signed the

Ostrów Agreement The Ostrów or Astrava Agreement (, , ) was a treaty between Jogaila (Władysław II Jagiełło), King of Poland and Grand Duke of Lithuania, and his cousin Vytautas the Great, signed on 4 August 1392. The treaty ended the destructive Lithuanian ...

, and Vytautas became his regent of the Grand Duchy of Lithuania. The

was returned to Vytautas as his patrimony. As a compensation Skirgaila received a portion of

Volhynia Volhynia or Volynia ( ; see #Names and etymology, below) is a historic region in Central and Eastern Europe, between southeastern Poland, southwestern Belarus, and northwestern Ukraine. The borders of the region are not clearly defined, but in ...

and

Kiev Kyiv, also Kiev, is the capital and most populous List of cities in Ukraine, city of Ukraine. Located in the north-central part of the country, it straddles both sides of the Dnieper, Dnieper River. As of 1 January 2022, its population was 2, ...

since 1395. The circumstances surrounding his death are not entirely clear. He was interred in the

Kiev Pechersk Lavra The Kyiv Pechersk Lavra or Kyievo-Pecherska Lavra (), also known as the Kyiv Monastery of the Caves, is a historic lavra or large monastery of Eastern Christianity that gave its name to the Pecherskyi District where it is located in Kyiv. Sinc ...

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{{DEFAULTSORT:Skirgaila 1350s births 1397 deaths 14th-century regents Year of birth uncertain Grand dukes of Lithuania Gediminids Burials at Kyiv Pechersk Lavra

Biography

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